


Dean Winchester, A Ladies' Man™

by Cassie221b



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Angel Blades (Supernatural), Castiel Isn't Either, Castiel/Dean Winchester Mutual Pining, Dean Winchester Has a Crush on Castiel, Dean Winchester Has a Panty Kink, Dean Winchester is Not Heterosexual, Dean has a thing for knifes, Dom Castiel/Sub Dean Winchester, Dom/sub Play, F/M, Knifeplay, M/M, No Beta, Oral Sex, Prostate Massage, Rimming, Rough Oral Sex, Spoiler: They fuck, Top Castiel/Bottom Dean Winchester, kind of, slight edging, we die like men here
Language: English
Status: Completed
Published: 2021-01-21
Updated: 2021-01-21
Packaged: 2021-03-12 12:09:12
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,917
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28885155
Author URL: https://archiveofourown.org/users/Cassie221b/pseuds/Cassie221b
Summary: And then, of course, there was Cas. Castiel. An angel of the fucking Lord, man. He knew he had a thing for Cas pretty much the instant he walked into that damn barn, but now…fuck it, now he was in love. It had taken him a while to admit that to himself, and even longer to accept it. He’d been to Hell and Purgatory and probably everywhere in between, but dreaming of getting fucked into oblivion by an angel? God’s favorite angel, that is? That’s gotta have some heavy consequences, right?
Relationships: Benny Lafitte/Dean Winchester, Castiel/Dean Winchester, Dean Winchester/Original Female Character(s)
Kudos: 109





	Dean Winchester, A Ladies' Man™

Dean Winchester was a ladies’ man. He loved their curves, their soft skin and their smell. He’d grown to love their bodies once he hit puberty, and being raised basically by himself he started to explore them only shortly after that. He’d had sex for the first time at 15, and it went about as you’d imagine. He was nervous, and she didn’t even ask for his name before. It was awkward. Quick. He never saw her again. But after that disaster, he’d gotten better. Nowadays, he made sure every woman he was with knew his name. To make sure they know what to scream once they come, as he likes to say. And while he did certainly had fun every time he fucked some random woman he picked up at a bar, he’d always felt like something was missing. Sure, he had tried a plethora of things, many of which Sam had probably never even heard of. And hell yes, he had learned much about himself. Amy scratched his back open, Sherly made him fuck her in a public restroom, Marie wore a leash, Jenny called him Daddy (which he did not enjoy that much, thankyouverymuch). And then there were the others. Cassie tied him down and rode him until he begged her to let him cum, Bonnie spanked him and Rhonda made him try on her panties. He always liked sex, but he loved those times. Still, after all that, he missed something. He had never trusted any of those women enough to actually go into subspace for them, he never got to let go completely. After a few years, sex lacked…excitement. 

Dean Winchester was a ladies’ man, but very rarely, he had let himself be with a man. He never fully submitted to them either because all of those were one-night-stands anyway. He never even bottomed for them. He knew for a fact he liked it up his ass if the countless showers in lonely motel rooms were anything to go by. He loved doing that to himself, but he never actually with someone else. A girl, Julie, had wanted to try anal with him once. She even owned one of those strap-on dicks he’d only ever seen in porn. He declined. If he were to do that with someone else, he wanted the real thing. But even sex with men started to get boring after a while. It lacked…commitment. Feelings. 

Until Purgatory. He had searched for Cas, but Benny was with him. Purgatory was…different. Raw. One night, shortly before they finally found Cas, he had fucked Benny against one of the trees. And hell, he felt something for Benny back then. Nothing strong, that is, but still. However, Benny was a vampire. Dean’s a hunter. It wouldn’t have worked out. 

And then, of course, there was Cas. Cas. An angel of the fucking Lord, man. He knew he had a thing for Cas pretty much the instant he walked into that damn barn, but now…fuck it, now he was in love. It had taken him a while to admit that to himself, and even longer to accept it. He’d been to Hell and Purgatory and probably everywhere in between, but dreaming of getting fucked into oblivion by an angel while having his hands and feet tied to the bed? God’s favorite angel, that is? That’s gotta have some heavy consequences, right? Obviously, he’d never actually acted on those feelings. Cas didn’t feel that way, he probably didn’t even understand what being in love meant. Or at least that’s what Dean thought. And to be honest, Dean thought he didn’t know either. For quite a long time, actually. But then he met Cas. There were many instances where he felt something when he was with Cas, he’d just never been able to put his finger on what exactly it was. But the moment it hit him was when that dick Zachariah sent him to 2014. Looking at Cas, at what he had become, that had changed things. Anyway, he never would’ve thought he’d ever actually get to do something about that desire within him. That’s why he was kind of surprised at how the events had unfolded the day before. 

*flashback*

Dean’s breath was pushed out of his chest when Cas shoved him back against the wall in his room. He felt wet kisses along his chin, Cas slowly working his way up to his mouth. Dean whimpered. Just before Cas reached his lips, he backed away a bit. He raised his eyebrow, looked Dean straight in the eye and started to whisper. “If I say or do something you’re not comfortable with, tell me immediately. Give me a word.” 

“Death”, Dean said without hesitation. He was sure that wasn’t going to come up in conversation randomly, at least not in the bedroom. 

Cas nodded, then his lips were on Dean’s. Dean responded passionately. Their kisses were messy, wild, raw. Neither of them thought about the consequences of this. When Dean felt Cas’ tongue against his teeth, he groaned. “Cas, please- “, he begged between kisses.

Cas, however, had no intention of getting anywhere near Dean's crotch just yet. Instead, his mouth left Dean's. Slowly, he started to work his way down the hunter's neck, leaving small marks along his way. After Dean's flannel had been successfully discarded, Castiel tore open his t-shirt. Dean's eyes widened for a second, but only until Cas' attention was on his neck again. When Cas began to tease Dean's nipples with his fingers, Dean's knees gave in. He felt himself getting hard. Thankfully, Cas had pinned him to the wall with his body. 

"Getting weak already, Dean?", Cas asked. " Do you know how easy it'd be for me to smite you? Do you know how much power I hold?"

Dean held his eyes close and nodded. Of course he knew. But still- "Show me, Cas. Show me how easy it would be for you to kill me. Show me my place, Cas. Please."

Cas looked at Dean for a second, but then we just went along with it. They had talked about this; they knew their limits and expectations. He could do this. For Dean. For himself. He reached for the angel blade that was conveniently placed on the desk next to them. "Alright. But first, strip.", he ordered. 

Dean couldn't recall ever getting out of his pants as fast as he just did. He threw them across the room and waited. When they made eye contact again, Cas smirked mischievously. "Kneel."

Dean complied happily. He fell to his knees in front of Cas, whose pants had started to get really tight as well. His head was now directly in front of the angel's cock and Dean looked up at Cas. 

"Such a good boy, Dean.", Cas said. He let his thumb run over Deans bottom lip. "And so beautiful. Want me to fuck that pretty mouth of yours?"

Dean nodded. This was already better than all of the fantasies he's had over the past years. Cas pulled his hair roughly. "Speak. I asked you a question, boy."

"Sorry, Sir. Yes, Sir. Please-", was all Dean managed at this point. He pulled the zipper of Cas’ pants open, somehow not at all surprised to find that his angel hadn’t been wearing underwear. As soon as Cas’ mouth sprung free, Dean cupped Cas’ balls with his hands and started to work his cock with his mouth. After letting his angel’s dick slide across his tongue from base to tip, he started to suck the tip into his mouth repeatedly until he grew more confident. He grabbed the base of Cas’ dick and swallowed him down, He hollowed his cheeks out and started humming some Led Zeppelin. Cas moaned at that. Moments after that, Dean went completely still and looked at Cas’ face, his lips still stretched around Cas. He felt Cas’ fingers in his hair and moaned deep in his throat when Cas started to move. He fucked into Dean’s mouth roughly, not at all caring that Dean started to choke. Dean, however, was having the time of his life. He tastes Cas’ precum in his mouth, the salty taste of it smeared across his tongue. 

He hollowed his cheeks out once again and started playing with his tongue a bit, which earned him a deep groan from his partner. And then, all too quickly in Dean’s humble opinion, Cas pulled out. His face was flushed and his pupils were blown wide, much to Dean’s satisfaction. “Turn around”, Cas ordered as soon as his breathing had evened out a little. 

Once again, Dean did what he was told. He stood up and turned around, his hands against the wall and his legs spread a little. He closed his eyes. Next thing he knew, Cas’ tongue was licking and nipping at his hole. Dean bit his bottom lip and moaned. 

Cas loved the taste of Dean. He loved the way the ring of muscles slowly gave in the more he toyed with it, the way Dean’s muscles contracted around his tongue an most of all, he loved the way Dean was moaning and keening at him. He reached for the bottle of lube he had placed next to them earlier, opened the cap and spread some of it on his finger. Slowly but surely, he started to insert his index finger into Dean instead of his tongue. Dean pressed his hips back in an attempt to get Cas’ finger deeper into him. “Be patient, Dean, and you shall be rewarded.”, Cas said. Dean didn’t manage to respond, however, because Cas had hit his sweet spot. He screamed out Cas’ name and kept begging for more as Cas hit his prostate repeatedly. Cas worked his way up to three fingers painfully slow with Dean having to stop himself from coming then and there more than once. Cas added a fourth finger and pulled out shortly after. 

“Ready?”, he asked. “Yes, Sir.”, Dean keened. 

Cas positioned himself behind Dean and pushed in. As soon as both of them had adjusted to the feeling of Cas literally being inside of Dean, he started to move. Slow at first, but his thrusts quickly got faster and more violent, hitting Dean’s prostate over and over again. Dean was shaking in Cas’ arms, and just when Dean thought he couldn’t take any more, Cas pulled out that damn angel blade again and held it against Dean’s throat. “See? That’s how easy it’d be.” And that was it. Dean came with a shout, his cum painting his stomach and the wall in front of him. 

Cas felt Dean clench around him and immediately knew he was close. He slammed in one more time and reached his own peak just in time with Dean. 

After they had come down from their high, Cas threw the angel blade to the ground, picked Dean up and carried him towards the bed. He grabbed some tissues, a glass of water and an additional blanket, got rid of his clothes and cuddled Dean on the bed. He handed Dean the glass of water, which was emptied in a matter of seconds. While Dean drank, he started to wipe Dean clean of their cum. “I love you, you know?”, Cas muttered as he pulled the blanket above their naked forms. “mhmm, love you too, Cas”, Dean mumbled already half asleep. Cas smiled, hugged Dean from behind and closed his eyes.


End file.
